Pyridyl



United States Patent 3,042,680 w-DI(PYRIDYL)-ALKANE DERIVATIVES 0Fl-ARYL-Z-AMEJO-ALKANES Kurt Thiele, Frankfurt am Main, Germany, assignorto Deutsche Goldund Silber-Scheideanstalt vormais Roessler, Frankfurt amMain, Germany No Drawing. Filed Nov. 13, 1961, Ser. No. 152,009

Claims priority, application Germany Nov. 18, 1960 3 Claims. (ill.260-296) The present invention relates to novel compounds of the formulaR1 CH R;

NE s l Ra-JJ-CHQ and their salts. In such formula: R; and R signifyhydrogen or the same or different lower alkyl groups, Alk signifies analkylene radical containing 2 to 4 carbon atoms of which 1 .or 2 carbonatoms form the bridge between the CH group and the NH group, R and Rsignify hydrogen or the same or different lower alkyl groups, R and Rsignify hydrogen or the same or different halogen atoms, such aschlorine or bromine, hydroxy groups or lower alkoxy groups, such asmethoxy and ethoxy. These compounds possess valuable pharmaceuticalproperties and particularly have a stimulating action on the centralnervous system and a coronary dilating action.

The compounds according to the invention can be produced by reacting adipyridyl methane of the formula in the presence of an alkalinecondensing agent.

The compounds according to the invention can also be prepared byreductively condensing a compound of the formula with a compound of theformula Furthermore the compounds can be prepared by reducing a compoundof the formula R1 R: \\N 0'11: ('10 10 i i R5 for example, with lithiumaluminum hydride. The following examples will serve to illustrateseveral embodiments of the invention.

Example 1 40.8 g. of di-(2-pyridyl)-methane were diluted with 180 cc. ofbenzene and 20.3 g. of a 50% sodamide in benzene suspension addedthereto. The mixture was then boiled under reflux for 4 hours.Thereafter, 36 g. of 1-phenyl- Z-w-brOmo-ethylamino propane dissolved in180 cc. of benzene were added dropwise and the mixture again refiuxedfor 4 hours. The reaction mixture was decomposed with Water whilecooling with ice, the benzene layer separated off and the aqueous layerextracted with chloroform. The solvent layers were combined and afterthe solvents were distilled oi the residue was fractionated undervacuum. After the excess di-(2-pyridyl)- methane had distilled over asfirst runnings, 24 g. .of N- (3-phenyl propyl-(2))-1,1-di-(2pyridyl)-propyl-(3)- amine of the formula distilled at 210 228 C. undera pressure of 1.5 mm. Hg. This base solidified upon being rubbed to formcrystals having a melting point of 6970 C. The free base was convertedinto the hydrochloride with HCl dissoolved in isopropanol. |Forpurification the salt was dissolved in acetone and recrystallized byaddition of ether. The resulting crystals had a melting point of 130-131C.

Example 2 86 g. of u-pyridyl-a-picolyl-(T)-methane were dissolved in 375cc. of benzene and refluxed with 39 g. of a 50% sodamide solution inbenzene for 4 hours. Thereafter, 75 g. of 1-phenyl-2-w-bromoethylaminopropane dissolved in 375 cc. of benzene were added and the mixturerefluxed for another 4 hours. Water was then added to the reactionmixture while cooling and the benzene layer separated off. The aqueouslayer was extracted with benzene and the combined benzene layers 5 driedand processed as in Example 1. After a first running of excessu-pyridyl-u-picolyl-(Z)-me-thane 47 g. of N-(3)-phenyl propyl(2'))-1-(2-pyridyl) -1-(6-methyl- 3 2-pyridyl)-propy l-(3)-amine of theformula distilled over at 204-208 C. under a pressure of 0.05 mm. Hg.The monohydrochloride of the free base had a melting point of 146-147 C.

' Example 3 'In a way similar to Example 1 the compound N-(3'- p-chlorophenyl propyl (2') )-1,1-di-(2-pyridy1)-propyl(3)-amine was prepared;The compound is an oil with a boiling point of 201 to 210 C. at apressure of 0.5 mm. Hg.

I claim: a 1. A compound 'of the formula N N i 11TH R5 7 3. A compoundof the formula No references cited;

1. A COMPOUND OF THE FORMULA